Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 51, Pages 14450-14463Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201101615
Keywords
azoles; C-H activation; coupling reactions; density functional calculations; reaction mechanisms
Categories
Funding
- Johnson & Johnson Industry
- CNRS
- CRUNCH network, INSA
- University of Rouen
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Both base-assisted non-concerted metallation-deprotonation (nCMD) and concerted metallation-deprotonation (CMD) have been identified as two potent operating mechanisms in palladium-catalysed direct C-H coupling of oxazole and thiazole-4-carboxylate esters with halides through base-and solvent-effect experiments. Novel C2- and C5-selective CMD direct arylation procedures in oxazole- and thiazole-4-carboxylate series were then designed by controlling the balance between electronic and steric factors. Notably, charge interactions between the palladium catalyst and substrate were identified as a parameter for controlling selectivity and reducing the impact of steric factors in the CMD reaction.
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